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Harlingen

$150+ Cheap flights from Chicago (CHI) to Harlingen, TX (HRL)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HRL
oct. 15 — oct. 221
mer. 10/15
mer. 10/22
1 adult, Economy
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Cheap flight deals from Chicago to Harlingen

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Harlingen (HRL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated septembre 15, 2025.

Round-trip from

$251
(American Airlines)

One-way from

$150
(Delta)

Popular in

November

Cheapest in

April

Average price

$471
From Chicago (CHI) to Harlingen Valley Intl
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One-way flight from Chicago (CHI) to Harlingen Valley Intl
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Highest demand for flights based on searches. 1% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Chicago to Harlingen

Cheapest flights from Chicago to Harlingen
Explore the most affordable flight options available from Chicago to Harlingen. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septembre 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 11/811:46 amORD - HRL
1 stop6h 24mAmerican Airlines
mar. 11/116:40 pmHRL - ORD
1 stop4h 57mAmerican Airlines
Deal found 9/14$251
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 10/14:20 pmORD - HRL
1 stop5h 05mSouthwest
lun. 10/67:00 amHRL - ORD
1 stop6h 05mSouthwest
Deal found 9/15$319
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 11/711:46 amORD - HRL
1 stop6h 24mAmerican Airlines
mar. 11/116:40 pmHRL - ORD
1 stop4h 57mAmerican Airlines
Deal found 9/14$334
This Sun Country Air deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 12/3111:45 amORD - HRL
1 stop23h 08mSun Country Air
dim. 1/411:49 amHRL - ORD
1 stop7h 01mSun Country Air
Deal found 9/15$372
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/299:00 amORD - HRL
1 stop7h 13mUnited Airlines
ven. 10/35:00 amHRL - ORD
1 stop6h 05mUnited Airlines
Deal found 9/13$379
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 10/123:10 pmORD - HRL
1 stop7h 55mSouthwest
dim. 10/196:50 amHRL - ORD
1 stop9h 35mSouthwest
Deal found 9/14$384
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 11/87:10 amORD - HRL
2 stops12h 29mUnited Airlines
mar. 11/115:00 pmHRL - ORD
1 stop7h 15mUnited Airlines
Deal found 9/14$403
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 10/92:20 pmORD - HRL
1 stop8h 58mUnited Airlines
dim. 10/125:17 pmHRL - ORD
1 stop6h 57mUnited Airlines
Deal found 9/15$412
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 9/184:20 pmORD - HRL
1 stop5h 10mSouthwest
sam. 9/207:25 amHRL - ORD
1 stop7h 00mSouthwest
Deal found 9/14$439
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 11/76:20 pmORD - HRL
2 stops16h 39mUnited Airlines
mar. 11/115:00 pmHRL - ORD
1 stop7h 15mUnited Airlines
Deal found 9/14$441

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Harlingen that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated septembre 15, 2025.
Use the filters below to find and compare flights from Chicago to Harlingen that are best for you.

Fly from

Chicago

Fly to

Harlingen

Route

Depart

Return

Price

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

mer. 10/1

4:20 pm-9:25 pm

1 stop5h 05m

Harlingen Valley Intl

lun. 10/6

7:00 am-1:05 pm

1 stop6h 05m

$319

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

ven. 11/7

11:46 am-6:10 pm

1 stop6h 24m

Harlingen Valley Intl

mar. 11/11

6:40 pm-11:37 pm

1 stop4h 57m

$334

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

mer. 12/31

11:45 am-10:53 am

1 stop23h 08m

Harlingen Valley Intl

dim. 1/4

11:49 am-6:50 pm

1 stop7h 01m

$372

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

lun. 9/29

9:00 am-4:13 pm

1 stop7h 13m

Harlingen Valley Intl

ven. 10/3

5:00 am-11:05 am

1 stop6h 05m

$379

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

dim. 10/12

3:10 pm-11:05 pm

1 stop7h 55m

Harlingen Valley Intl

dim. 10/19

6:50 am-4:25 pm

1 stop9h 35m

$384

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

jeu. 10/9

2:20 pm-11:18 pm

1 stop8h 58m

Harlingen Valley Intl

dim. 10/12

5:17 pm-12:14 am

1 stop6h 57m

$412

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

ven. 11/7

6:20 pm-10:59 am

2 stops16h 39m

Harlingen Valley Intl

mar. 11/11

5:00 pm-12:15 am

1 stop7h 15m

$441

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

mar. 3/10

1:10 pm-12:04 am

2 stops10h 54m

Harlingen Valley Intl

mer. 3/11

5:50 am-10:58 am

1 stop5h 08m

$492

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

dim. 10/12

6:08 am-2:43 pm

1 stop8h 35m

$150

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

ven. 9/26

4:50 pm-11:18 pm

1 stop6h 28m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 14 results
1
2

Best time to book a flight from Chicago to Harlingen

Have a flexible travel schedule? Discover the best time to fly to Harlingen from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Harlingen

What is the cheapest month to book a flight from Chicago to Harlingen, Texas?

Currently, April is the cheapest month in which you can book a flight from Chicago to Harlingen, Texas (average of $267). Flying from Chicago to Harlingen, Texas in June is currently the most expensive (average of $382). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to HRL?

Find hourly flight availability from Chicago to Harlingen. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septembre 15, 2025.

It’s optimal to fly from Chicago to Harlingen, Texas in the evening. By choosing this option you can save up to 20% on the cost of your flight, compared to a flight in the morning.

What’s the top layover airport for flights from Chicago to Harlingen, Texas?

Share of 1-stop round-trip flights from Chicago to Harlingen, Texas chosen by Cheapflights users in the past 12 months, using the same layover each way.

Austin (AUS) – chosen by Cheapflights users on 93% of 1-stop itineraries from Chicago to Harlingen, Texas on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Harlingen, Texas?

Average round-trip fare for 1-stop flights from Chicago to Harlingen, Texas, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Austin (AUS) is the most affordable 1-stop option, with an average round-trip price of $261.

What’s the fastest layover option from Chicago to Harlingen, Texas?

Shortest average travel time for 1-stop one-way flights from Chicago to Harlingen, Texas, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Austin (AUS) have the shortest average one-way travel time for 1-stop routes: 4h 55m.

Which airport typically offers the quickest layover for flights from Chicago to Harlingen, Texas?

Average layover duration for 1-stop one-way flights from Chicago to Harlingen, Texas, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Houston (IAH) offer the fastest connection on this route, with an average layover time of 1h 10m.

Reviews of airlines servicing Harlingen

Get insights into the airlines that provide service to Harlingen. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Harlingen. Reviews last updated septembre 15, 2025.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American Airlines from Chicago to Harlingen to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Chicago to Harlingen. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Harlingen from Chicago?

    Located just 3.7 mi from the city center, Harlingen Valley Intl is the airport most travelers will use when flying to Harlingen from Chicago. Booking flights from Chicago to Valley Intl (HRL) should be relatively easy as there are 0 daily inbound flights from Chicago from 3 different airlines.

  • How long is the flight from Chicago to Harlingen, Texas?

    There are many flights that can get you from Chicago to Harlingen, Texas in 5h 05m. Fly via Southwest, American Airlines, or Sun Country Air to get the fastest option. Chicago and Harlingen, Texas are separated by a distance of 1220 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago to Harlingen, Texas round-trip?

    According to our current data, Southwest ($208), United Airlines ($226), and American Airlines ($267) offers the cheapest pricing from Chicago to Harlingen, Texas. Users have found that Southwest is 45% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Chicago to Harlingen, Texas one-way?

    The cheapest airlines for a one-way flight from Chicago to Harlingen, Texas are Delta ($150), United Airlines ($229), and Southwest ($285).

  • Can I find deals for flights from Chicago to Harlingen that include hotel bookings?

    Yes. In addition to deals on Chicago to Harlingen flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Harlingen?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Harlingen.

  • Can I find deals for business class flights from Chicago to Harlingen?

    Yes. Cheapflights offers flight deals from Chicago to Harlingen by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Harlingen, Texas?

    Currently, April is the cheapest month in which you can book a flight from Chicago to Harlingen, Texas (average of $267). Flying from Chicago to Harlingen, Texas in June is currently the most expensive (average of $382). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Chicago to Harlingen

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Chicago to Harlingen

Discover the top 3 airlines that operate flights from Chicago to Harlingen. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated septembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$208Average$382FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$226Average$445FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$267Average$385FlexibilityNo cancel feeOn-time71%

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